5 Big, Brave Choices to Lead You to Successful Self-Employment

Self-employment. It’s the dream of many, but the hard-fought-for reality of far fewer.

If you find yourself in the latter group and wondering how you can plan for and switch to self-employment, make these five big and brave choices. You’ll put yourself on the path to a successful work-for-yourself career.

1. Work a thankless job you’ll be thankful for later

There’s no denying that long hours, low pay and seemingly unreachable expectations can be overwhelming in the workplace, but you may just find yourself thankful for the experience later on. Here’s why: thankless jobs often result in exponential skill growth and knowledge expansion. In the right situation, you can learn more in one or two years than you ever possibly could in several years working in a more laid-back office atmosphere.

What’s more, the practical time and project management lessons you learn will serve you well in your self-employed future. When you have your own business, you need to know how to spend your time wisely in order to get the highest return on investment. That isn’t an easy lesson to learn, and it’s one that’s best absorbed with a steady paycheck hitting the bank account each week.

So, how do you find the right job to learn from? Be picky. Very, very picky. In these high-stress environments, it’s rarely possible to ask for professional development or responsibilities in new areas. Instead, there will be an expectation of perfection in regard to your actual job description. As such, it’s important to read descriptions and duties carefully, confirm them during the interview process and be very forthright about what you want and expect out of the position.

Here’s the thing: very few employers expect the people that take these types of positions to stay longer than two to three years. This means that there’s no shame in being clear about what you want to learn, see and do during your time in this job.

My inside scoop: I regularly worked 60-70 hour weeks in my first job out of college. Tons of travel. A ton of responsibility. I regularly cried on my sofa, burying myself in ice cream. But, guess what? I nailed it, and nearly 10 years later, I use the skills I learned in that job every day working for myself.

2. Dedicate two weekends a month to your growing your side business

But, news flash: If you’re serious about working for yourself, you need to start dedicating a few weekends each month to develop, grow and sustain your freelance business. This is the truth no one wants to hear when they dream of being self-employed: sacrifice is essential.

In the beginning, you’ll be working on the basics: choosing a name, creating a business plan, developing a website, working on select projects for free or very little pay and generating buzz about your services. Even these basic tasks take time and dedication. In fact, you’ll very quickly realize that a few nights a week are necessary in addition to a few weekends.

Plan these growth weekends out: set goals, make lists and always make honest checks on your progress. Most likely, you’ll be amazed at how far two weekends a month can get you on your path to success.

My inside scoop: There were plenty of instances where I didn’t take a real day off for a month or more because I quickly learned how high-impact my weekends could be. Was it ideal? Of course not. But I rapidly grew my business and exceeded even my own (very high) expectations.

3. Create a professional development plan…and stick to it like glue

As mentioned earlier in this article, you can’t depend on an employer to provide all of the professional development that you need. What’s more, when you create your own development plan, you are in the driver’s seat to decide what’s most important for you and your career. It’s imperative for your success that you create a professional development plan for yourself—and make sure that it happens.

From small lessons gained from reading a few industry articles a week to big time commitments like certifications and classes, a professional development plan can help you gain an edge on your competition and secure the business you need to grow your client base. When you’re just getting started, stick to free resources and tutorials. As you become more focused and interested in certain topics, you can hone in on select and smart paid opportunities.

My inside scoop: In the online world, things are always changing. As such, my professional development plan is a cornerstone of my business. There’s always something I can learn or get better at. Anyone who isn’t learning isn’t competing in today’s market.

4. Shack up in a less-than-ideal living situation

One of the biggest concerns when going to work for yourself is how you’ll pay the bills. And, what’s the biggest bill we all have? Housing. One of the quickest ways to ease the housing bill burden and grow that rainy day fund fast is to figure out a living situation that eases the financial burden.

Look, no one wants to move back home with mom and dad or join five other roommates in a one-bedroom apartment, but sometimes downsizing your living space is the best thing you can do for your self-employment prospects. You may—nay, you will—be shocked at the emotional and psychological burden that lifts from your shoulders when you aren’t so concerned with paying a big rent bill every month. You will have a level of strategic and creative clarity the likes of which you’ve never seen.

My inside scoop: Want to hear something funny? Selling my house and living in my childhood bedroom was a turning point in my business. For six months, money wasn’t a factor. I just worked, grew and planned. I would repeat it in a heartbeat if I ever needed to.

5. Start just before you’re ready

If you wait for the “right moment” or until you’re “really ready,” then you should expect to never find your way to self-employment or location independence. That’s because you’re never really quite ready to take a total leap of faith.

The key is to make sure you’re prepared to take the big step to self-employment. Now, you can read lots of articles with lists about what it means to be prepared or ready to be fully self-employed (check below for a handy list), but at the end of the day, you need to make a checklist that addresses your needs and concerns.

Some signs that you’re prepared:

A comfortable amount of cushion in the bank. This will be one month for some and one year for others. We all have a “comfort point” when it comes to the rainy day fund.

A happy and growing client base. One or two solid clients is great, but always be looking for ways to grow. Business changes fast, and you don’t want to put all of your eggs in one basket.

A gut feeling. If something inside is telling you that now is the time, then yes, you are ready. Go with it.

My inside scoop: Would I have loved to have had a few more years of total self-employment before I moved abroad to Italy? Of course. But at the end of the day, I just had to put faith in myself and take the plunge. I’m so glad I did.

Dana Leavy-Detrick

There is no perfect time, as Kate said. But what worked for me, and others, is to have an exit strategy in place that looks at your personal, business and startup expenses for the first 6-12 months. If you have a plant to stay afloat, you can develop your business in a smart and strategic manner, instead of out of a place of desperation to pay your bills.

Terri Howard

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